Patent GB-992961-A (GB)
Title: Process for the manufacture of amino acid derivatives
IPC: C07K1/08
Filed: 1961-07-28
Abstract: The invention comprises N-acyl-N1-aminoacyl-hydrazines, derivatives of such hydrazines with protected amino, hydroxy, mercapto or carboxyl groups, and acid addition salts of such hydrazines or their derivatives, wherein "aminoacyl" denotes the acyl radical of a natural a -aminocarboxylic acid and the "N-acyl" radical denotes a carboxylic, carbonic or sulphonic acid acyl group.  The above compounds, and also N-acyl-hydrazines, derivatives thereof with protected amino, hydroxy, mercapto or carboxyl groups, and acid addition salts of such N-acyl-hydrazines or their derivatives, are prepared by reacting a hydrazine or an N-acyl-hydrazine in the presence of a carboxylic acid with an a -amino acid-N-carboxyanhydride or a derivative thereof having a protected amino, hydroxy, mercapto or carboxyl group.  A suitable carboxylic acid is glacial acetic acid, while the reaction may also be conducted in the presence of an organic solvent such as dioxan.  The examples describe the preparation of N-acetyl-N1-D,L-phenylalanyl - hydrazine, N - benzoyl - N1 - D,L-phenylalanyl - hydrazine, N - para - toluene-sulphonyl - N1 - D,L - phenylalanyl - hydrazine, N - tertiary - butyloxycarbonyl - N1 - D - leucylhydrazine, N - tertiary - butyloxycarbonyl - N1 - glycyl - hydrazine, N - tertiary - butyl - oxycarbonyl - N1 - D,L - valyl - hydrazine, N - tertiary - butyloxycarbonyl - N1 - D,L-phenylalanyl - hydrazine, N - tertiary - butyloxycarbonyl - N1 - D - phenylalanyl - hydrazine, N - tertiary - butyloxycarbonyl - N1 - L - prolyl - hydrazine, N - carbobenzoxy - glycyl-N1 - D - phenylalanyl - hydrazine, N - carbobenzoxy - D - valyl - N1 - D - valyl - hydrazine, N - benzoyl - glycyl - N1 - D,L - phenylalanyl-hydrazine, N - benzoyl - glycyl - N1 - D - phenylalanyl - hydrazine, N - L - valyl - N1-L - valyl - hydrazine, N - benzoyl - glycyl - N1-glycyl - hydrazine, N - benzoyl - glycyl - N1-D-alanyl - hydrazine, N - benzoyl - glycyl-glycyl - N1 - D,L - phenylalanyl - hydrazine, N - carbobenzoxyglycyl - N1 - glycyl - hydrazine, N - carbobenzoxyglycyl - N1 - D,L - phenylalanyl - hydrazine, N - carbobenzoxyglycyl-N1 - L - phenylalanyl - hydrazine, N - carbobenzoxy - glycyl - N1 - D - valyl - hydrazine, N - carbobenzoxy - glycyl - N1 - L - prolylhydrazine, N - carbobenzoxy - glycylglycyl-N - D,L - phenylalanyl - hydrazine, N1 - carbobenzoxyglycylglycyl - N1 - D - phenylalanyl-hydrazine, N - carbobenzoxy - L - valyl - N1-glycyl - hydrazine, N - carbobenzoxy - L-valyl - N1 - (o-acetyl) - tyrosyl - hydrazine, N - carbobenzoxy - L - valyl - N1 - tyrosylhydrazine, N - carbobenzoxy - L - phenylalanyl - N1 - D - valyl - hydrazine, N - tosylglycyl - N1 - D - phenylalanyl - hydrazine, N-tosyl - L - prolyl - N1 - D - phenylalanyl-hydrazine, N - tosyl - glycyl - N1 - D - valyl-hydrazine, N - para - nitrophenyl - N1 - D,L-phenylalanyl - hydrazine, N - phenyl - N1-D,L - phenylalanyl - hydrazine, N - analinoformyl - N1 - D,L - phenylalanyl - hydrazine, and the hydrochlorides, hydrates, alcoholates and trifluoroacetates of such compounds. Specification 992,962 is referred to.